New easy approach to the synthesis of 2,5-disubstituted and 2,4,5-trisubstituted 1,3-oxazoles. The reaction of 1-(methylthio)acetone with nitriles

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3026-3032

  Herrera, Antonio ^a   Martínez Alvarez, Roberto ^a   Ramiro, Pedro ^a   Molero, Dolores ^a   Almy, John ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3-OXAZOLES; RANEY NICKEL; SUBSTITUTED BENZENES; TRIFLIC ANHYDRIDE;

BENZENE; CATALYSTS; NITRILE RESINS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION KINETICS;

ACETONE;

1 (METHYLTHIO) 2 OXOPROPYL TRIFLATE; 1 (METHYLTHIO)ACETONE; 2 PHENYL 5 METHYL 4 (METHYLSULFONYL) 1,3 OXAZOLE; 2 PHENYL 5 METHYL 4 (METHYLTHIO) 1,3 OXAZOLE; 5 METHYL 2 (4 METHOXYPHENYL) 1,3 OXAZOLE; 5 METHYL 2 [4 [5 METHYL 4 (METHYLTHIO) 1,3 OXAZOL 2 YL]PHENYL] 4 (METHYLTHIO) 1,3 OXAZOLE; ACETONE; NICKEL; NITRILE; OXAZOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

ACETONE; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MOLECULAR STRUCTURE; NITRILES; OXAZOLES; OXIDATION-REDUCTION; SULFIDES; SULFUR; TEMPERATURE;

EID: 33645766934     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052619v     Document Type: Article

References (38)

1. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303-2304.
2. Cruz-Monserrate, Z.; Vervoort, H. C.; Bai, R. L.; Newman, D.; Howell, S. B.; Los, G.; Mullaney, J. T.; Williams, M. D.; Pettit, G. R.; Fenical, W.; Hamel, E. Mol. Pharmacol. 2003, 63, 1273-1280.
3. Kobayashi, J.; Tsuda, M.; Fuse, H.; Sasaki, T.; Mikami, Y. J. Nat. Prod. 1997, 60, 150-154.
4. Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765-4770.
5. Nicolaou, K. C.; Chen, D. Y. K.; Huan, X.; Ling, T.; Bella, M.; Snyder, S. A. J. Am. Chem. Soc. 2004, 126, 12888-12896.
6. Davies, J. R.; Kane, P. D.; Moody, C. J. J. Org. Chem. 2005, 70, 7305-7316.
7. Li, Y.-M.; Milne, J. C.; Madison, L. L.; Kolter, R.; Walsh, C. T. Science 1996, 274, 1188-1190.
8. Palmer, D. C.; Taylor, E. C. Oxazoles: Synthesis, Reactions and Spectroscopy, Parts A & B, Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 2004; Vol. 60.
9. Cornforth, J. W.; Cornforth, R. H. J. Chem. Soc. 1947, 96-102.
10. Yokohama, M.; Menjo, Y.; Watanabe, M.; Togo, H. Synthesis 1994, 1467-1470.
11. (a) Robinson, R. J. Chem. Soc. 1909, 95, 2176-2174.
12. (b) Brain, C. T.; Paul, J. M. Synlett 1999, 1642-1644.
13. Doyle, M. P.; Buhro, W. E.; Davidson, J. G.; Elliot, R. C.; Hoekstra, J. W.; Oppenhuizen, M. J. Org. Chem. 1980, 45, 3657-3664.
14. Prager, R. H.; Smith, J. A.; Weber, B.; Williams, C. M. J. Chem. Soc., Perkin Trans, 1 1997, 2665-2672.
15. (a) Pulici, M.; Quartier, F.; Felder, E. R. J. Comb. Chem. 2005, 7, 463-473.
16. (b) Keni, M.; Tepe, J. J. J. Org. Chem. 2005, 70, 4211-4213.
17. Lee, Y. R.; Yeon, S. H.; Seo, Y.; Kim, B. S. Synthesis 2004, 2787-2798.
18. Milton, M. D.; Inada, Y.; Nishibayashi, Y.; Uemura, S. Chem. Commun. 2004, 23, 2712-2713.
19. Stephen, A.; Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 23, 4391-4394.
20. Cai, X. H.; Yang, H. J.; Zhang, G. L. Synthesis 2005, 1569-1571.
21. Lee, J. C.; Hong, T. Tetrahedron Lett. 1997, 38, 8959-8960.
22. Varma, R. S.; Kumar, D. J. Helerocycl. Chem. 1998, 55, 1533-1534.
23. Lee, J. C.; Song, I. G. Tetrahedron Lett. 2000, 41, 5891-5894.
24. Lee, J. C.; Choi, H. J.; Lee, Y. C. Tetrahedron Lett. 2003, 44, 123-125.
25. García Martínez, A.; Herrera Fernández, A.; Moreno Jímenez, F.; García Fraile, A.; Subramanian, L. R.; Hanack, M. J. Org. Chem. 1992, 57, 1627-1630.
26. García Martínez, A.; Herrera Fernández, A.; Molero Vilchez, D.; Hanack, M.; Subramanian, L. R. Synthesis 1992, 1053-1054.
27. (a) Molero Vilchez, D. PhD Dissertation, Universidad Complutense de Madrid, Spain, 1993.
28. (b) Ramiro Pérez, P. PhD Dissertation, Universidad Complutense de Madrid, Spain, 2004.
29. Porter, Q. N. Mass Spectrometry of Heterocyclic Compounds; John Wiley & Sons: New York, 1985.
30. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1987, 52, 3413-3420.
31. Shafer, C. M.; Molinski, T. F. J. Org. Chem, 1998, 63, 551-555.
32. Hartner, F. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 3.
33. (a) Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds; Springer: Heidelberg, 2003.
34. (b) ACD/HNMR and ACD/CNMR Predictor, version 5.09; www.acdlabs.com; Advanced Chemistry Development, Inc.: Toronto, Canada, 2001.
35. (a) García, A.; Herrera, A.; Martínez-Alvarez, R.; Teso, E.; García, A.; Osío, J.; Pargada, L. Tetrahedron Lett. 1987, 38, 1929-1932.
36. (b) García, A.; Herrera, A.; Martínez-Alvarez, R.; Teso, E.; García, A.; Osío, J.; Pargada, L.; Unanue, R.; Hanack, M.; Subramanian, L. R. J. Heterocycl. Chem. 1988, 25. 1237-1241.
37. (c) Hanack, M.; Subramania, L. R. Houben-Weyl, Carbokationen, Carbokationen-Radikale. Band E19c; Georg Thieme: Stuttgart, 1990; p 98.
38. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman Scientific & Technical: Essex, 1989.